Taking Initiative With A Guy I Liked Totally Paid Off & I’ve Never Been Happier

I appreciate chivalry as much as anyone but I got sick of waiting for the guy to instigate things if there was some important step I wanted to take in our relationship—or if I wanted to start a relationship in the first place. I decided to stop waiting for guys to come to me and started taking charge. It was a change that seriously paid off.

  1. I asked him out. I had my eye on this guy I’d known for awhile and we were finally both single for the first time since we’d met. There’d always been a sort of mutual attraction between us, or so I’d felt, so I thought, why not ask him to dinner? Even though I could’ve been wrong, I took the risk so that I’d never have to wonder if he was thinking the same thing. Turns out, he was too shy to ask me out so he gladly accepted my invitation and appreciated the fact that I had the courage to speak up.
  2. I planned the first date as well as several others. I figured since I’d already done the asking, I may as well take the next step and actually plan the date too. He had some ideas in mind, but I kindly told him to save them for another time because this one was all on me. I made the reservations, I picked him up and I paid. I thought the whole thing may make him a little uncomfortable but he was more than on board.
  3. I openly flirted with him. I’ve always been a little shy when it comes to flirting, not to mention pretty awkward. I took this as an opportunity to brush up on my skills and I pulled out all the classic moves like yawning and putting my arm around him during a movie. It made us both laugh and he seemed to really love the attention.
  4. I initiated the “define the relationship” conversation. After several weeks of dating, I could tell it was getting serious. In the past, I would have casually mentioned more couple-y things we could be doing together to prompt the guy I was dating into having “The Talk” but instead of being coy, I decided to simply tell him I thought we should discuss where things were going. He’d been thinking the same thing and it opened up the lines of communication for other future discussions as well.
  5. I brought up some heavy topics. Once relationships get going, inevitably some hard things are going to surface. Normally, I’m afraid to bring up things like exes or relationship baggage because I worry they may cause a fight and fighting terrifies me. Since I’d been rather bold during the beginning of our relationship, it gave me the confidence I needed to continue that streak. I did have to pick my battles but if it was worth discussing, I trusted my gut and jumped in.
  6. I broke the ice during awkward moments. Considering both of us had a string of bad relationships in the past, it was often a topic of conversation between our families and also our friends. There were times the teasing would go a little too far and instead of sitting there keeping quiet and trying to be polite, I spoke up or made a joke to ease the tension. He really appreciated it and it made things way less awkward and uncomfortable. Why not have a sense of humor?
  7. I didn’t wait for him to say “I love you” first. I sometimes feel like maybe I should’ve let my boyfriend have this one but I felt it so I said it. It was really hard because he didn’t say it back right away and truthfully, that hurt. When he finally did say it, though, I knew he meant it and wasn’t just regurgitating my words.
  8. When the time was right, I suggested moving in together. Now, in some ways, this was somewhat of a mutual decision. We’d gone back and forth for months about whether the timing was right and if merging our lives on this new level was practical or not but we never really got anywhere. Finally, after much thinking about it on my own, I told him flat out I thought we should take the plunge. He agreed and that was that. We didn’t overthink it—we just acted and took the necessary steps to make it work. Lucky for us, it totally did and it upped our commitment that much more.
  9. I wasn’t afraid to spell out what I wanted. This was always my struggle with every boyfriend I had in the past. I never wanted to ask for too much or come off needy so I would just say everything was fine even if there was something missing. I decided it was time to smash that pattern for good. I made sure that I wasn’t being dramatic or emotional, but if something felt off, I mentioned it. If I felt I got a cold response to something difficult we were talking about, I told him. I invited him to do the same so we both knew it was safe to be honest and wow, I can’t tell you how freeing it was to finally not be afraid to have a voice.
jordan is a writer from salt lake city who enjoys a good steak, her dog, and conversations about how radiohead is awesome. she hopes to be a talking head on some VH1 pop-culture show someday and can curate a playlist for any occasion. when she grows up she wants to be an olsen twin.